DE526803C - Process for the iodination of 2-aminopyridine - Google Patents
Process for the iodination of 2-aminopyridineInfo
- Publication number
- DE526803C DE526803C DED51822D DED0051822D DE526803C DE 526803 C DE526803 C DE 526803C DE D51822 D DED51822 D DE D51822D DE D0051822 D DED0051822 D DE D0051822D DE 526803 C DE526803 C DE 526803C
- Authority
- DE
- Germany
- Prior art keywords
- aminopyridine
- solution
- amps
- iodopyridine
- electrolyzed
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Description
Verfahren zur Jodierung von 2-Aminopyridin Es wurde gefunden, daß 2-Aminopyridin durch elektrolytisch abgeschiedenes Jod leicht jodierbar ist. In Ausübung der Erfindung verfährt man z. B. derart, daß eine wässerige Lösung von Alkalijodid, z. B. eine Kaliumjodidlösung, mit 2-Aminopyridin versetzt und die Lösung unter Bedingungen elektrolysiert wird, bei welchen anodisch Jod in Freiheit gesetzt wird. Man kann der Lösung gegebenenfalls noch Stoffe zufügen, welche, wie z. B. Alkalicarbonat, Alkalihydroxyd o. dgl., befähigt sind, frei werdenden Jodwasserstoff zu binden. Der Zusatz dieser Stoffe kann von vornherein oder auch während der Durchführung des Vorganges z. B. anteilweise erfolgen.Process for the iodination of 2-aminopyridine It has been found that 2-aminopyridine can be easily iodized by electrolytically deposited iodine. In Exercise of the invention one proceeds z. B. such that an aqueous solution of Alkali iodide, e.g. B. a potassium iodide solution, mixed with 2-aminopyridine and the solution is electrolyzed under conditions in which anodically iodine is set free will. You can optionally add substances to the solution, which, such. B. Alkali carbonate, alkali hydroxide or the like, are capable of releasing hydrogen iodide to tie. These substances can be added from the outset or during the implementation the process z. B. be done in part.
Die Durchführung des Verfahrens erfolgt vorteilhafterweise unter lebhafter Durchmischung des Gutes, z. B. durch kräftiges Rühren. Es hat sich weiterhin als vorteilhaft erwiesen, zwecks Vermeidung von Perjodidbildung mit niedriger anodischer Stromdichte zu arbeiten. Die Jodierung erfolgt bereits bei gewöhnlicher Temperatur. Durch Arbeiten bei erhöhter Temperatur wird der Verlauf der Reaktion beschleunigt. Beispiele i. Eine Lösung, bestehend aus ig g 2-Aminopyridin, 33g Kaliumjodid, ioo ccm Wasser und 25o ccm Methylalkohol, wird 7,3 Stunden mit 2 Amp. bei einer anodischen Stromdichte von 0,05 Amp./cm2 unter Umrühren bei einer Temperatur von o bis 5° elektrolysiert. Nach Beendigung der Elektrolyse wird der klar braune Elektrolyt im Vakuum eingedampft. Man erhält ii g 2-Amino-5-jodpyridin. Zurückgewonnen werden ii g 2-Aminopyridin.The process is advantageously carried out under brisk Mixing of the goods, e.g. B. by vigorous stirring. It continued to be called Proven to be advantageous in order to avoid periodide formation with a lower anodic value Current density to work. The iodination takes place at normal temperature. The course of the reaction is accelerated by working at an elevated temperature. Examples i. A solution consisting of ig g 2-aminopyridine, 33g potassium iodide, ioo cc of water and 25o cc of methyl alcohol, is 7.3 hours with 2 amps. with an anodic Current density of 0.05 Amp./cm2 electrolyzed with stirring at a temperature of 0 to 5 °. After the electrolysis has ended, the clear brown electrolyte is evaporated in vacuo. Two g of 2-amino-5-iodopyridine are obtained. II g of 2-aminopyridine are recovered.
2. Eine Lösung von ig g 2-Aminopyridin, 33 g Kaliumjodid und 25 g Natriumbicarbonat in ioo ccm Wasser und 25o ccm Methanol wird 7,5 Stunden mit 2 Amp. bei einer anodischen Stromdichte von 0,05 Amp./cm2 unter Rühren bei einer Temperatur von o bis 5 ° elektrolysiert. Durch Eindampfen des Elektrolyten im Vakuum erhält man 12 g 2-Amino-5-jodpyridin.2. A solution of ig g of 2-aminopyridine, 33 g of potassium iodide and 25 g of sodium bicarbonate in 100 cc of water and 25o cc of methanol is used for 7.5 hours at 2 amps at an anodic current density of 0.05 amps / cm2 with stirring electrolyzed at a temperature of 0 to 5 °. Evaporation of the electrolyte in vacuo gives 12 g of 2-amino-5-iodopyridine.
3. Eine Lösung von ig g 2-Aminopyridin, 33 g Kaliumjodid und 25 g Natriumbicarbonat in loo ccm Wasser und 250 ccm Methanol wird 8 Stunden mit 1,5 Amp. bei einer anodischen Stromdichte von 0,05 Amp./cm2 unter Rühren elektrolysiert. Die Temperatur wird auf 3o bis 35' gehalten. Durch Eindampfen der Elektrolyten im Vakuum gewinnt man ii g 2-Amino-5-j odpyridin.3. A solution of ig g of 2-aminopyridine, 33 g of potassium iodide and 25 g of sodium bicarbonate in 100 cc of water and 250 cc of methanol is electrolyzed for 8 hours at 1.5 amps at an anodic current density of 0.05 amps / cm2 with stirring . The temperature is kept at 3o to 35 ' . By evaporating the electrolytes in vacuo, ii g of 2-amino-5-iodopyridine are obtained.
q.. Eine Lösung von ig g 2-Aminopyridin, 33 g Kaliumjodid in 350 ccm Wasser wird 7 Stunden mit 2 Amp. bei einer anodischen Stromdichte von o,o5 Amp./cm2 und einer Temperatur von o bis 5 ° unter Rühren elektrolysiert. Durch Eindampfen des Elektrolyten im Vakuum erhält man 7,7 g 2 Amino-5-jodpyridin.._ 12, Die Erfindung ermöglicht die Gewinnung des therapeutisch wertvo11en 2-Amino-5-jodpyridins auf verhältnismäßig sehr einfachem Wege unter Erzielung guter Ausbeuten. Bei sachgemäßer Durchführung des Verfahrens findet eine gleichzeitige Bildung von Di- oder Polyjodderivaten nicht statt.q .. A solution of ig g of 2-aminopyridine, 33 g of potassium iodide in 350 ccm of water is electrolyzed for 7 hours at 2 amps at an anodic current density of 0.05 amps / cm2 and a temperature of 0 to 5 ° with stirring. By evaporating the electrolyte in vacuo, 7.7 g of 2-amino-5-iodopyridine are obtained . The invention enables the therapeutically valuable 2-amino-5-iodopyridine to be obtained in a relatively simple manner with good yields. If the process is carried out properly, di- or polyiodo derivatives will not be formed at the same time.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DED51822D DE526803C (en) | 1926-12-02 | 1926-12-02 | Process for the iodination of 2-aminopyridine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DED51822D DE526803C (en) | 1926-12-02 | 1926-12-02 | Process for the iodination of 2-aminopyridine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE526803C true DE526803C (en) | 1931-06-10 |
Family
ID=7053683
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DED51822D Expired DE526803C (en) | 1926-12-02 | 1926-12-02 | Process for the iodination of 2-aminopyridine |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE526803C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2521544A (en) * | 1946-07-13 | 1950-09-05 | American Cyanamid Co | Iodinating amino pyrimidines and amino pyridines |
-
1926
- 1926-12-02 DE DED51822D patent/DE526803C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2521544A (en) * | 1946-07-13 | 1950-09-05 | American Cyanamid Co | Iodinating amino pyrimidines and amino pyridines |
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